Old Town Winchester

Winchester

The Courthouse in Winchester, Virginia.
The Courthouse in Winchester, Virginia.
Handley Library
A nice 3 block outdoor downtown shopping area with dining and bars also.
Holiday shopping in Winchester.

Popular places to visit

Gardens at Glen Burnie House.

Museum of the Shenandoah Valley

You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley
Jim Barnett park

Jim Barnett Park

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.

Jim Barnett Park

Shenandoah Valley Discovery Museum

You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah Valley Discovery Museum

Bright Box Theater

Enjoy a performance at Bright Box Theater, a popular theatre in Winchester. While in this walkable area, you can savour the top-notch restaurants.

Bright Box Theater

Old Court House Civil War Museum

You can study the exhibits at Old Court House Civil War Museum, a museum with a story of its own, during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Old Court House Civil War Museum

Handley Regional Library

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.

Handley Regional Library

Top hotels in Old Town Winchester

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is S$175 per night from 1 Mar to 2 Mar
S$175
1 Mar - 2 Mar
includes taxes & fees
Stay at this spa hotel in Winchester. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
9.4/10 Exceptional! (1,005 reviews)
Fantastic

Reviewed on 19 Feb, 2026

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
The price is S$145 per night from 24 Feb to 25 Feb
S$145
24 Feb - 25 Feb
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (2,272 reviews)
Very clean Staff was amazing at check in

Reviewed on 21 Feb, 2026

La Quinta Inn & Suites by Wyndham Winchester
Quality Inn Winchester

Quality Inn Winchester

2.5 out of 5
1601 Martinsburg Pike Winchester VA
The price is S$116 per night from 28 Feb to 1 Mar
S$116
28 Feb - 1 Mar
includes taxes & fees
Stay at this hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
9.2/10 Wonderful! (1,002 reviews)
Staff were friendly and helpful. Room was clean, spacious and the bed was comfortable. Easy check in, convenient parking and the area felt safe

Reviewed on 21 Feb, 2026

Quality Inn Winchester
Sleep Inn & Suites Winchester near University

Sleep Inn & Suites Winchester near University

2.5 out of 5
140 Costello Dr Winchester VA
The price is S$110 per night from 15 Mar to 16 Mar
S$110
15 Mar - 16 Mar
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (1,007 reviews)
Room was clean

Reviewed on 20 Feb, 2026

Sleep Inn & Suites Winchester near University
TownePlace Suites by Marriott Front Royal

TownePlace Suites by Marriott Front Royal

3 out of 5
5 Caroline Drive Front Royal VA
Fully refundableReserve now, pay when you stay
The price is S$180 per night from 27 Feb to 28 Feb
S$180
27 Feb - 28 Feb
includes taxes & fees
Stay at this business-friendly hotel in Front Royal. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (564 reviews)
Don’t stay here ICE is staying here

Reviewed on 20 Feb, 2026

TownePlace Suites by Marriott Front Royal
Hampton Inn Winchester-University/Mall Area

Hampton Inn Winchester-University/Mall Area

2.5 out of 5
640 East Jubal Early Drive Winchester VA
The price is S$146 per night from 8 Mar to 9 Mar
S$146
8 Mar - 9 Mar
includes taxes & fees
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,001 reviews)
I sent a message to the Hotel as we had to head directly home - as my wife was feeling ill; but I'm not sure the Hotel received my message and canceled the reservation. I'm surprised I didn't get a response.

Reviewed on 18 Feb, 2026

Hampton Inn Winchester-University/Mall Area
See all 370 properties in Old Town Winchester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

The Annual Holiday Sale

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Other neighbourhoods around Old Town Winchester

Buildings and streets in the historic part of the ancient city of Winchester in Virginia.

Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester Historic District

Old Town Winchester